CA2591094A1 - Process for the manufacture of 1,2-dichloroethane - Google Patents
Process for the manufacture of 1,2-dichloroethane Download PDFInfo
- Publication number
- CA2591094A1 CA2591094A1 CA002591094A CA2591094A CA2591094A1 CA 2591094 A1 CA2591094 A1 CA 2591094A1 CA 002591094 A CA002591094 A CA 002591094A CA 2591094 A CA2591094 A CA 2591094A CA 2591094 A1 CA2591094 A1 CA 2591094A1
- Authority
- CA
- Canada
- Prior art keywords
- fraction
- ethylene
- mixture
- products
- advantageously
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 76
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 33
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 95
- 239000005977 Ethylene Substances 0.000 claims abstract description 95
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 238000005336 cracking Methods 0.000 claims abstract description 34
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 27
- 238000005406 washing Methods 0.000 claims abstract description 26
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 23
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 22
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000012670 alkaline solution Substances 0.000 claims abstract description 15
- 238000000197 pyrolysis Methods 0.000 claims abstract description 15
- 238000010791 quenching Methods 0.000 claims abstract description 13
- 230000003647 oxidation Effects 0.000 claims abstract description 12
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 12
- 230000000171 quenching effect Effects 0.000 claims abstract description 12
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 10
- 239000000470 constituent Substances 0.000 claims abstract description 9
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 52
- 210000002196 fr. b Anatomy 0.000 claims description 45
- 210000003918 fraction a Anatomy 0.000 claims description 37
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 239000007800 oxidant agent Substances 0.000 claims description 31
- 238000000926 separation method Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 22
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 20
- 239000001294 propane Substances 0.000 claims description 18
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 16
- 239000001273 butane Substances 0.000 claims description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 14
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 210000000540 fraction c Anatomy 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 239000004800 polyvinyl chloride Substances 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
- 239000001282 iso-butane Substances 0.000 claims description 2
- 239000003345 natural gas Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 51
- 239000005708 Sodium hypochlorite Substances 0.000 description 19
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 14
- 239000010949 copper Substances 0.000 description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 13
- 235000013844 butane Nutrition 0.000 description 13
- 229910052802 copper Inorganic materials 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 229910052749 magnesium Inorganic materials 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 238000010526 radical polymerization reaction Methods 0.000 description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 6
- 229910015400 FeC13 Inorganic materials 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000007792 gaseous phase Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- -1 sulphide ion Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000012674 dispersion polymerization Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910013470 LiC1 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000001112 coagulating effect Effects 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 235000015073 liquid stocks Nutrition 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- NHYCGSASNAIGLD-UHFFFAOYSA-N Chlorine monoxide Chemical class Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 229910001902 chlorine oxide Inorganic materials 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical class Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MYVTXUAIVALIHC-UHFFFAOYSA-N sodium;copper Chemical compound [Na+].[Cu] MYVTXUAIVALIHC-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
- C07C17/152—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons
- C07C17/156—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons of unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
- C07C19/043—Chloroethanes
- C07C19/045—Dichloroethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/04—Chloro-alkenes
- C07C21/06—Vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/02—Monomers containing chlorine
- C08F14/04—Monomers containing two carbon atoms
- C08F14/06—Vinyl chloride
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0413873A FR2880019B1 (fr) | 2004-12-23 | 2004-12-23 | Procede de fabrication de 1,2-dichloroethane |
| FR04.13873 | 2004-12-23 | ||
| FR0503253A FR2883870B1 (fr) | 2005-04-01 | 2005-04-01 | Procede de fabrication de 1,2-dichloroethane |
| FR0503252 | 2005-04-01 | ||
| FR05.03253 | 2005-04-01 | ||
| FR05.03252 | 2005-04-01 | ||
| PCT/EP2005/057046 WO2006067191A1 (en) | 2004-12-23 | 2005-12-21 | Process for the manufacture of 1,2-dichloroethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2591094A1 true CA2591094A1 (en) | 2006-06-29 |
Family
ID=36011022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002591094A Abandoned CA2591094A1 (en) | 2004-12-23 | 2005-12-21 | Process for the manufacture of 1,2-dichloroethane |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20080108856A1 (no) |
| EP (1) | EP1831138A1 (no) |
| JP (1) | JP2008525378A (no) |
| KR (1) | KR20070094936A (no) |
| AR (1) | AR052833A1 (no) |
| AU (1) | AU2005318152B2 (no) |
| BR (1) | BRPI0518551A2 (no) |
| CA (1) | CA2591094A1 (no) |
| EA (1) | EA013840B1 (no) |
| EG (1) | EG25197A (no) |
| MX (1) | MX2007007778A (no) |
| MY (1) | MY169678A (no) |
| NO (1) | NO20073247L (no) |
| TW (1) | TW200626524A (no) |
| WO (1) | WO2006067191A1 (no) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
| CA2532367C (en) | 2003-07-15 | 2013-04-23 | Grt, Inc. | Hydrocarbon synthesis |
| US20050171393A1 (en) | 2003-07-15 | 2005-08-04 | Lorkovic Ivan M. | Hydrocarbon synthesis |
| US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
| US20060100469A1 (en) | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
| KR101335397B1 (ko) | 2006-02-03 | 2013-12-02 | 지알티, 인코포레이티드 | 할로겐으로부터 가벼운 기체를 분리하는 방법 |
| AP2673A (en) | 2006-02-03 | 2013-05-23 | Grt Inc | Continuous process for converting natural gas to liquid hydrocarbons |
| FR2902784B1 (fr) | 2006-06-23 | 2008-09-05 | Solvay | Procede de fabrication de 1,2-dichloroethane |
| FR2902785B1 (fr) | 2006-06-26 | 2008-08-08 | Solvay | Procede de fabrication de 1,2-dichloroethane |
| FR2902786B1 (fr) | 2006-06-26 | 2008-08-29 | Solvay | Procede de fabrication de 1,2-dichloroethane |
| FR2902787B1 (fr) | 2006-06-26 | 2008-09-05 | Solvay | Procede de fabrication de 1,2-dichloroethane |
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| EP2130814A1 (en) | 2008-06-03 | 2009-12-09 | SOLVAY (Société Anonyme) | Process for the manufacture of at least one ethylene derivative compound |
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| WO2011067231A1 (en) | 2009-12-03 | 2011-06-09 | Solvay Sa | Process for the manufacture of at least one ethylene derivative compound |
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| US8198495B2 (en) | 2010-03-02 | 2012-06-12 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
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| US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
| US8829256B2 (en) | 2011-06-30 | 2014-09-09 | Gtc Technology Us, Llc | Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons |
| US8802908B2 (en) | 2011-10-21 | 2014-08-12 | Marathon Gtf Technology, Ltd. | Processes and systems for separate, parallel methane and higher alkanes' bromination |
| EP2594547A1 (en) | 2011-11-17 | 2013-05-22 | Solvay Sa | Process for the manufacture of at least one ethylene derivative compound from bioethanol |
| US9193641B2 (en) | 2011-12-16 | 2015-11-24 | Gtc Technology Us, Llc | Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems |
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| JPS4932841B1 (no) * | 1966-04-15 | 1974-09-03 | ||
| IT946065B (it) * | 1971-11-17 | 1973-05-21 | Sir Soc Italiana Resine Spa | Perfezionamenti nei procedimenti per la preparazione di dicloroe tano |
| DE3044854A1 (de) * | 1980-11-28 | 1982-07-01 | Hoechst Ag, 6000 Frankfurt | "verfahren zur herstellung von 1,2-dichlorethan" |
| US4417986A (en) * | 1981-03-13 | 1983-11-29 | Mobil Oil Corporation | Process for reducing the chemical oxygen demand of spent alkaline reagents |
| FR2690155B1 (fr) * | 1992-04-21 | 1994-05-27 | Atochem Elf Sa | Procede de preparation du chlorure de vinyle par ultrapyrolyse du 1,2 dichloroethane. |
| WO1996035653A1 (en) * | 1995-05-08 | 1996-11-14 | Ppg Industries, Inc. | Promotion of 1,2-dichloroethane pyrolysis with chloral and/or chloral hydrate |
| IN192223B (no) * | 1995-12-28 | 2004-03-20 | Du Pont | |
| GB2312672B (en) * | 1996-05-01 | 1998-10-28 | Stone & Webster Eng Ltd | Spent caustic treatment |
| EA003072B1 (ru) * | 1998-09-16 | 2002-12-26 | Джеймс К. Жанблан | Способ десульфурации |
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| DE19911078A1 (de) * | 1999-03-12 | 2000-09-21 | Krupp Uhde Gmbh | Verfahren zur Herstellung von VCM |
| DE10159615A1 (de) * | 2001-12-05 | 2003-06-12 | Basf Ag | Verfahren zur Herstellung von 1,2-Dichlorethan |
| FR2862238B1 (fr) * | 2003-11-14 | 2006-11-17 | Solvay | Catalyseur a base d'alumine contenant du titane et procede en phase gazeuse utilisant un tel catalyseur |
| US20070161830A1 (en) * | 2004-08-05 | 2007-07-12 | Solvay (Societe Anonyme) | Process for regenerating a hydrogenation catalyst |
-
2005
- 2005-12-21 CA CA002591094A patent/CA2591094A1/en not_active Abandoned
- 2005-12-21 JP JP2007547521A patent/JP2008525378A/ja active Pending
- 2005-12-21 WO PCT/EP2005/057046 patent/WO2006067191A1/en active Application Filing
- 2005-12-21 MX MX2007007778A patent/MX2007007778A/es unknown
- 2005-12-21 US US11/722,598 patent/US20080108856A1/en not_active Abandoned
- 2005-12-21 EA EA200701325A patent/EA013840B1/ru not_active IP Right Cessation
- 2005-12-21 AU AU2005318152A patent/AU2005318152B2/en not_active Ceased
- 2005-12-21 AR ARP050105417A patent/AR052833A1/es unknown
- 2005-12-21 KR KR1020077017001A patent/KR20070094936A/ko not_active Application Discontinuation
- 2005-12-21 EP EP05849766A patent/EP1831138A1/en not_active Withdrawn
- 2005-12-21 BR BRPI0518551-3A patent/BRPI0518551A2/pt not_active IP Right Cessation
- 2005-12-22 TW TW094145901A patent/TW200626524A/zh unknown
- 2005-12-22 MY MYPI20056163A patent/MY169678A/en unknown
-
2007
- 2007-06-17 EG EGNA2007000605 patent/EG25197A/xx active
- 2007-06-25 NO NO20073247A patent/NO20073247L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005318152A1 (en) | 2006-06-29 |
| EP1831138A1 (en) | 2007-09-12 |
| JP2008525378A (ja) | 2008-07-17 |
| WO2006067191A1 (en) | 2006-06-29 |
| AR052833A1 (es) | 2007-04-04 |
| MY169678A (en) | 2019-05-09 |
| EA200701325A1 (ru) | 2007-10-26 |
| BRPI0518551A2 (pt) | 2008-11-25 |
| AU2005318152B2 (en) | 2011-10-13 |
| US20080108856A1 (en) | 2008-05-08 |
| EG25197A (en) | 2011-11-14 |
| TW200626524A (en) | 2006-08-01 |
| EA013840B1 (ru) | 2010-08-30 |
| MX2007007778A (es) | 2007-08-21 |
| NO20073247L (no) | 2007-09-17 |
| KR20070094936A (ko) | 2007-09-27 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20131119 |